SML0282

Bexarotene

≥98% (HPLC)

• Synonym(s): 4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]benzoic acid, LGD-1069, SR-11247
• Empirical Formula (Hill Notation): C₂₄H₂₈O₂
• CAS Number: 153559-49-0
• Molecular Weight: 348.48
• MDL number: MFCD00932428
• UNSPSC Code: 41106305
• PubChem Substance ID: 329825290
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: ≥15 mg/mL (warmed)
• storage temp.: −20°C
• SMILES string: C=C(C1=CC=C(C(O)=O)C=C1)C2=C(C)C=C3C(C(C)(C)CCC3(C)C)=C2
• InChI: 1S/C24H28O2/c1-15-13-20-21(24(5,6)12-11-23(20,3)4)14-19(15)16(2)17-7-9-18(10-8-17)22(25)26/h7-10,13-14H,2,11-12H2,1,3-6H3,(H,25,26)
• InChI key: NAVMQTYZDKMPEU-UHFFFAOYSA-N
• Gene Information: human ... RXRA(6256) , RXRB(6257) , RXRG(6258)

Description

Application

Bexarotene has been used as retinoid x receptor (RXR) agonist:

• to study its effect on human oral squamous cell carcinoma (OSCC) cell lines
• to test for cooperative cell killing of cutaneous T cell lymphoma (CTCL) with 966
• as a standard in HPLC for determining its potential impurities in drug substances and drug products

Bexarotene has been used:

• to investigate its effects on the changes in renal, cardiac, hepatic, and pulmonary expression/activity of inducible nitric oxide synthase (iNOS) and CYP4F6
• to analyze the involvement of retinoid x receptor (RXR) homo or permissive heterodimers
• to study its potential impurities in drug substances and drug products

Biochem/physiol Actions

Bexarotene is a highly selective retinoid X receptor (RXR) agonist. It is an antineoplastic agent, already approved as an oral antineoplastic agent for cutaneous T cell lymphoma and being investigated against other cancers. A study has found that bexarotene in a mouse Alzheimer′s model lowered the most toxic form of β-amyloid peptide and increased cognitive ability. The activity in the mouse Alzheimer′s models are believed to be by activating PPARγ:RXR and LXR:RXR dimers which induces the expression of apoE and facilitates Aβ clearance and promotes microglial phagocytosis.

Bexarotene is used to treat breast cancer.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable